Senior Manager - B2B Sales Enablement

Staples Canada; Richmond Hill; Hybrid; CAD 110,000 - 150,000; Full time

Benefits offered by this job

Associate discount

Health and Dental benefits

RRSP/DPSP

Performance bonuses

Learning & Development programs

And more...

Job summary

Staples Canada seeks a Senior Manager - B2B Sales Enablement to drive end-to-end GTM readiness across its B2B org. You will lead enablement strategies, equipping sellers with tools, training, content, and knowledge to launch and scale strategic initiatives.

This leader oversees training, knowledge management, and seller-facing programs, partnering with Sales, Marketing, Merchandising and Operations to deliver seamless GTM activation in a fast-paced environment. Hybrid work in Richmond Hill.

Qualifications

• Bachelor’s degree preferred in Business, Marketing or related field.
• Strong expertise in Sales Enablement, GTM execution and change management.
• Experience building scalable processes, playbooks and frameworks.
• Proven track record leading large-scale GTM launches or transformation initiatives.
• 5–7+ years in Sales Enablement, Sales Operations, Strategy or related roles.
• 3–5+ years of people leadership experience.

Responsibilities

• Lead end-to-end readiness planning and execution for major B2B initiatives.
• Define and operationalize a standardized GTM readiness framework.
• Partner with cross-functional stakeholders on launch priorities and execution plans.
• Oversee development and governance of seller-facing content.
• Ensure sellers are equipped to execute B2B go-to-market priorities.
• Oversee onboarding, training, and reinforcement programs via Sales Training Manager.
• Develop and execute the B2B Sales Enablement roadmap aligned to priorities.
• Establish scalable enablement models to improve productivity and performance.
• Define KPIs to measure enablement effectiveness.
• Continuously assess gaps and optimize enablement strategies.

Skills

Sales Enablement

GTM execution

Change management

Playbooks

Scalable processes

Leadership

Education

Bachelor’s degree

Job description

Title: Senior Manager - B2B Sales Enablement

Some Of What You Will Do

The Sr. Manager, B2B Sales Enablement is accountable for driving end-to-end Go-to-Market (GTM) readiness across Staples Canada’s B2B organization. This role leads to the development and execution of enablement strategies that ensure sellers are fully equipped with the tools, training, content, and knowledge required to successfully launch and scale strategic initiatives.

This leader oversees core enablement functions including training, knowledge management, and seller-facing program execution, while partnering cross-functionally with Sales, Marketing, Merchandising, and Operations to deliver seamless GTM activation.

Responsibilities

• Lead end-to-end readiness planning and execution for all major B2B initiatives (e.g., product launches, pricing changes, platform enhancements, SMB programs).
• Define and operationalize a standardized GTM readiness framework (playbooks, timelines, readiness checkpoints, success metrics).
• Partner with cross-functional stakeholders to ensure alignment on launch priorities, dependencies, and execution plans.
• Oversee development and governance of seller-facing content, ensuring accuracy, consistency, and accessibility.
• Accountable for ensuring sellers are equipped to successfully execute B2B go-to-market priorities.
• Oversee onboarding, training, and reinforcement programs delivered through the Sales Training Manager.
• Develop and execute the B2B Sales Enablement roadmap aligned to strategic priorities (e.g., SMB growth, digital adoption, AI/Agentforce activation).
• Establish scalable enablement models to improve seller productivity, adoption, and performance.
• Define KPIs to measure enablement effectiveness (e.g., adoption rates, time-to-readiness, seller productivity).
• Continuously assess gaps and optimize enablement strategies based on feedback and performance insights.

Some Of What You Need

• Bachelor’s degree in Business, Marketing, or related field preferred.
• Strong expertise in Sales Enablement, GTM execution, and change management.
• Ability to operate in fast-paced, transformation-driven environments.
• Experience building scalable processes, playbooks, and frameworks.
• Proven track record of leading large-scale GTM launches or transformation initiatives.
• 5-7+ years of experience in Sales Enablement, Sales Operations, Strategy, or related roles.
• 3–5+ years of people leadership experience.
• Experience in B2B sales environments (preferred; mid-market/SMB exposure is an asset).

Physical Demands/working Conditions

• Office environment – Hybrid, with 4 days onsite in Richmond Hill, subject to the hybrid policy (for most positions).

Some Of What You Will Get

• Associate discount
• Health and Dental benefits
• RRSP/DPSP
• Performance bonuses
• Learning & Development programs
• And more...

About Us

We value transparency in our hiring processes. Please note, artificial intelligence may be used in certain stages to screen, assess, or select applicants, however, a human reviewer makes all final decisions. This posting is for an existing vacancy.

About The Team

At Staples Canada we are dynamic, inspiring partners to our customers and the communities in which we live. As The Working and Learning Company, we inspire people to work smarter, learn more and grow every day. We’re looking for curious, approachable, and passionate individuals who love finding solutions. If that’s you, let’s work, learn, and grow together.

We are building an inclusive and diverse team

Staples Canada is continuously working towards creating an inclusive and diverse work environment. We welcome, value and thrive on perspectives and contributions from backgrounds that vary by race, gender, sexual orientation, gender identity or expression, lifestyle, age, educational background, national origin, religion or physical ability. If you have a disability or special need that requires accommodation, please let us know.